4-Hydroxy-4-isopropenyl-3-isopropoxy-2-methyl-cyclobut-2-enone | 304467-82-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-Hydroxy-4-isopropenyl-3-isopropoxy-2-methyl-cyclobut-2-enone
• 英文别名: 4-Hydroxy-2-methyl-3-propan-2-yloxy-4-prop-1-en-2-ylcyclobut-2-en-1-one；4-hydroxy-2-methyl-3-propan-2-yloxy-4-prop-1-en-2-ylcyclobut-2-en-1-one
• CAS: 304467-82-1
• 化学式: C₁₁H₁₆O₃
• 分子量: 196.246
• InChiKey: JMGGQZHYZHZDQV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-Hydroxy-4-isopropenyl-3-isopropoxy-2-methyl-cyclobut-2-enone 在 potassium carbonate 、 silver(l) oxide 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 3.0h， 生成 (2E,4E)-4-methoxy-2,5,8-trimethyl-3-propan-2-yloxycycloocta-2,4-dien-1-one
  参考文献：
  名称：

  Reaction of 4-methoxy-4-(1-methylethenyl)-2-cyclobutenone derivatives with 2-lithiopropene and α-lithiostyrene: synthesis of eight-membered ring carbocycles

  摘要：

  2-Alkyl- or phenyl-substituted 4-methoxy-4-(1-methylethenyl)-2-cyclobutenones react with 2-lithiopropene or alpha-lithiostyrene to produce 4-methoxy-2,4-cyclooctadienones in moderate yield, accompanied by varying amounts of 4-methoxy-4-(1-methylethenyl)-2-cyclohexenones. The reaction is general for 2-alkyl substituted 4-methoxy-4-(1-methylethenyl)-2-cyclobutenones. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)01173-4
• 作为产物：
  描述：

  isopropenyllithium 、 3-(1-methylethoxy)-4-methylcyclobut-3-ene-1,2-dione 在 氯化铵 作用下， 以 四氢呋喃 为溶剂， 以70%的产率得到4-Hydroxy-4-isopropenyl-3-isopropoxy-2-methyl-cyclobut-2-enone
  参考文献：
  名称：

  Reaction of 4-methoxy-4-(1-methylethenyl)-2-cyclobutenone derivatives with 2-lithiopropene and α-lithiostyrene: synthesis of eight-membered ring carbocycles

  摘要：

  2-Alkyl- or phenyl-substituted 4-methoxy-4-(1-methylethenyl)-2-cyclobutenones react with 2-lithiopropene or alpha-lithiostyrene to produce 4-methoxy-2,4-cyclooctadienones in moderate yield, accompanied by varying amounts of 4-methoxy-4-(1-methylethenyl)-2-cyclohexenones. The reaction is general for 2-alkyl substituted 4-methoxy-4-(1-methylethenyl)-2-cyclobutenones. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)01173-4

文献信息

• Nickel-catalyzed ring-opening of α-hydroxycyclobutenones with a remarkable ligand effect
  作者：Songsong Gao、Xiangdong Hu

  DOI：10.1039/c7cc03340k

  日期：——

  A Ni-catalyzed ring-opening of α-hydroxycyclobutenones is reported herein. A remarkable ligand effect was observed during transformations following the ring-opening. The employment of PPh3 leads to the formation of 2-furanones 2 through a migration of an alkoxyl group, and 2-furanones 3 were generated through a migration of hydrogen in the presence of Xantphos, affording a divergent approach to 2-furanones

  本文报道了Ni催化的α-羟基环丁烯酮的开环。开环后的转化过程中观察到了显着的配体效应。PPh3的使用通过烷氧基的迁移导致形成2-呋喃酮2，而在Xantphos的存在下通过氢的迁移生成了2-呋喃酮3，从而提供了一种具有多种功能的2-呋喃酮的发散方法。组。
• Stereocontrolled [4+1] Annulation of α-Hydroxycyclobutenones: Synthesis of Polysubstituted Cyclopentenones
  作者：Xu Mao、Peidong Song、Yu Hao、Zezhong Sun、Xiangdong Hu

  DOI：10.1002/adsc.201600670

  日期：2016.12.7

  A stereocontrolled [4+1] annulation of α‐hydroxycyclobutenones has been disclosed. For the first time, α‐hydroxycyclobutenones have been proven as facile diene precursors for [4+1] annulation. Meanwhile, the reported transformation presents a concise synthetic route to polysubstituted cyclopentenones with high stereoselectivity.

  已经公开了α-羟基环丁烯酮的立体控制的[4 + 1]环。首次证明了α-羟基环丁烯酮是用于[4 + 1]环化的简便二烯前体。同时，报道的转化为具有高立体选择性的多取代的环戊烯酮提供了简明的合成路线。